TW200902020A - Heterocyclic antiviral compounds - Google Patents

Heterocyclic antiviral compounds Download PDF

Info

Publication number: TW200902020A
Authority: TW; Taiwan
Prior art keywords: methyl; butyl; dimethyl; spiro; oxa
Prior art date: 2007-03-29

Application number

TW097110847A

Other languages

English (en)

Chinese (zh)

Inventor

Chris Richard Melville

David Mark Rotstein

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-03-29

Filing date

2008-03-26

Publication date

2009-01-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39535486&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW200902020(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2008-03-26 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2009-01-16 Publication of TW200902020A publication Critical patent/TW200902020A/zh

Links

150000001875 compounds Chemical class 0.000 title claims description 171
125000000623 heterocyclic group Chemical group 0.000 title description 3
230000000840 anti-viral effect Effects 0.000 title 1
238000011282 treatment Methods 0.000 claims abstract description 30
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 11
208000030507 AIDS Diseases 0.000 claims abstract description 10
210000000056 organ Anatomy 0.000 claims abstract description 9
208000006673 asthma Diseases 0.000 claims abstract description 8
-1 methyl-cyclohexyl-methyl Chemical group 0.000 claims description 133
239000002253 acid Substances 0.000 claims description 47
150000003839 salts Chemical class 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
241000725303 Human immunodeficiency virus Species 0.000 claims description 25
239000003814 drug Substances 0.000 claims description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 20
208000015181 infectious disease Diseases 0.000 claims description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
239000007789 gas Substances 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
230000001225 therapeutic effect Effects 0.000 claims description 9
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
241000237858 Gastropoda Species 0.000 claims description 6
206010052779 Transplant rejections Diseases 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
LSBIUXKNVUBKRI-UHFFFAOYSA-N 4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC=N1 LSBIUXKNVUBKRI-UHFFFAOYSA-N 0.000 claims description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229910052736 halogen Chemical group 0.000 claims description 5
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
230000000670 limiting effect Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000002689 soil Substances 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 3
208000011623 Obstructive Lung disease Diseases 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000003566 oxetanyl group Chemical group 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000006001 difluoroethyl group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
238000001228 spectrum Methods 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
230000002265 prevention Effects 0.000 claims 2
150000003573 thiols Chemical class 0.000 claims 2
KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 claims 2
IXOFDKUWTXPQFC-UHFFFAOYSA-N 3-(trifluoromethyl)-1,2-oxazole Chemical compound FC(F)(F)C=1C=CON=1 IXOFDKUWTXPQFC-UHFFFAOYSA-N 0.000 claims 1
KGQJOPJSIZEIDD-UHFFFAOYSA-N 4-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=NC(S)=C1 KGQJOPJSIZEIDD-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 claims 1
229910001873 dinitrogen Inorganic materials 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical group COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
239000007787 solid Substances 0.000 abstract description 19
102000004274 CCR5 Receptors Human genes 0.000 abstract description 18
108010017088 CCR5 Receptors Proteins 0.000 abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
208000024908 graft versus host disease Diseases 0.000 abstract description 3
206010038997 Retroviral infections Diseases 0.000 abstract description 2
150000003053 piperidines Chemical class 0.000 abstract description 2
208000035475 disorder Diseases 0.000 abstract 2
208000011580 syndromic disease Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 311
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 276
235000019439 ethyl acetate Nutrition 0.000 description 156
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 110
239000000243 solution Substances 0.000 description 103
239000000203 mixture Substances 0.000 description 79
238000000034 method Methods 0.000 description 66
210000004027 cell Anatomy 0.000 description 63
238000006243 chemical reaction Methods 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
238000004587 chromatography analysis Methods 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 30
101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 28
102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
239000002585 base Substances 0.000 description 25
239000002904 solvent Substances 0.000 description 23
239000004480 active ingredient Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
239000003795 chemical substances by application Substances 0.000 description 19
239000000284 extract Substances 0.000 description 19
238000009472 formulation Methods 0.000 description 19
102000019034 Chemokines Human genes 0.000 description 18
108010012236 Chemokines Proteins 0.000 description 18
238000003756 stirring Methods 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
239000011734 sodium Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 15
230000035605 chemotaxis Effects 0.000 description 15
239000003446 ligand Substances 0.000 description 15
239000012071 phase Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
102100032367 C-C motif chemokine 5 Human genes 0.000 description 14
108010055166 Chemokine CCL5 Proteins 0.000 description 14
239000004615 ingredient Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
238000000746 purification Methods 0.000 description 14
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
238000003556 assay Methods 0.000 description 13
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000013058 crude material Substances 0.000 description 12
230000000694 effects Effects 0.000 description 12
238000012360 testing method Methods 0.000 description 12
241000713772 Human immunodeficiency virus 1 Species 0.000 description 11
206010061218 Inflammation Diseases 0.000 description 11
239000005557 antagonist Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 11
230000004054 inflammatory process Effects 0.000 description 11
238000013508 migration Methods 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 10
229910000420 cerium oxide Inorganic materials 0.000 description 10
239000012528 membrane Substances 0.000 description 10
230000005012 migration Effects 0.000 description 10
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 10
239000000843 powder Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
206010003246 arthritis Diseases 0.000 description 9
230000027455 binding Effects 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
201000010099 disease Diseases 0.000 description 9
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
210000000265 leukocyte Anatomy 0.000 description 9
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
208000009386 Experimental Arthritis Diseases 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
210000001744 T-lymphocyte Anatomy 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000006260 foam Substances 0.000 description 8
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 8
210000004379 membrane Anatomy 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
230000037396 body weight Effects 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
235000018102 proteins Nutrition 0.000 description 7
102000004169 proteins and genes Human genes 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
239000000052 vinegar Substances 0.000 description 7
235000021419 vinegar Nutrition 0.000 description 7
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
108010023347 Met- RANTES Proteins 0.000 description 6
206010036790 Productive cough Diseases 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000000872 buffer Substances 0.000 description 6
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical group COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
210000001616 monocyte Anatomy 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
230000004044 response Effects 0.000 description 6
210000003802 sputum Anatomy 0.000 description 6
208000024794 sputum Diseases 0.000 description 6
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 5
XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 5
102100036011 T-cell surface glycoprotein CD4 Human genes 0.000 description 5
241000700605 Viruses Species 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
239000005667 attractant Substances 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
230000007910 cell fusion Effects 0.000 description 5
239000003067 chemokine receptor CCR5 antagonist Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
210000003979 eosinophil Anatomy 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000004927 fusion Effects 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
239000000137 peptide hydrolase inhibitor Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000007920 subcutaneous administration Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
239000003826 tablet Substances 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
102000009410 Chemokine receptor Human genes 0.000 description 4
108050000299 Chemokine receptor Proteins 0.000 description 4
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
239000007995 HEPES buffer Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 4
YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
229960004365 benzoic acid Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
230000031902 chemoattractant activity Effects 0.000 description 4
230000003399 chemotactic effect Effects 0.000 description 4
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000012091 fetal bovine serum Substances 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
230000008595 infiltration Effects 0.000 description 4
238000001764 infiltration Methods 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
238000001802 infusion Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000008101 lactose Substances 0.000 description 4
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
210000002540 macrophage Anatomy 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000007922 nasal spray Substances 0.000 description 4
229940097496 nasal spray Drugs 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
238000002953 preparative HPLC Methods 0.000 description 4
230000008569 process Effects 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
238000013268 sustained release Methods 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
PVCCNBXYARRUAT-UHFFFAOYSA-N (3-methoxycyclohexyl)methanol Chemical compound COC1CCCC(CO)C1 PVCCNBXYARRUAT-UHFFFAOYSA-N 0.000 description 3
KCDKSZWKVROYKI-UHFFFAOYSA-N (4-hydroxycyclohexyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CCC(O)CC1 KCDKSZWKVROYKI-UHFFFAOYSA-N 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
GWNOTCOIYUNTQP-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 GWNOTCOIYUNTQP-FQLXRVMXSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 3
108010036949 Cyclosporine Proteins 0.000 description 3
108010008165 Etanercept Proteins 0.000 description 3
208000031886 HIV Infections Diseases 0.000 description 3
229910004373 HOAc Inorganic materials 0.000 description 3
241000282412 Homo Species 0.000 description 3
101000946926 Homo sapiens C-C chemokine receptor type 5 Proteins 0.000 description 3
102100034349 Integrase Human genes 0.000 description 3
108060001084 Luciferase Proteins 0.000 description 3
239000005089 Luciferase Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
230000004913 activation Effects 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
229960001830 amprenavir Drugs 0.000 description 3
238000002832 anti-viral assay Methods 0.000 description 3
RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
230000004888 barrier function Effects 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003086 colorant Substances 0.000 description 3
239000006071 cream Substances 0.000 description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
238000011161 development Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
AYXBAIULRDEVAS-UHFFFAOYSA-N dimethyl-[[4-[[3-(4-methylphenyl)-8,9-dihydro-7h-benzo[7]annulene-6-carbonyl]amino]phenyl]methyl]-(oxan-4-yl)azanium;iodide Chemical compound [I-].C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(=O)NC=3C=CC(C[N+](C)(C)C4CCOCC4)=CC=3)C2=C1 AYXBAIULRDEVAS-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
210000002889 endothelial cell Anatomy 0.000 description 3
FKULPVKPKUIFHX-UHFFFAOYSA-N ethyl 4-(methoxymethoxy)cyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(OCOC)CC1 FKULPVKPKUIFHX-UHFFFAOYSA-N 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000013355 food flavoring agent Nutrition 0.000 description 3
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
230000006870 function Effects 0.000 description 3
BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
102000048160 human CCR5 Human genes 0.000 description 3
238000011534 incubation Methods 0.000 description 3
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 3
230000004968 inflammatory condition Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000012669 liquid formulation Substances 0.000 description 3
239000006210 lotion Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
210000000440 neutrophil Anatomy 0.000 description 3
229920006316 polyvinylpyrrolidine Polymers 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
230000000770 proinflammatory effect Effects 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 3
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 3
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229960001203 stavudine Drugs 0.000 description 3
229960005322 streptomycin Drugs 0.000 description 3
239000004291 sulphur dioxide Substances 0.000 description 3
235000010269 sulphur dioxide Nutrition 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
239000012730 sustained-release form Substances 0.000 description 3
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
238000001890 transfection Methods 0.000 description 3
238000002054 transplantation Methods 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
229960000523 zalcitabine Drugs 0.000 description 3
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 2
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical group C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
XEJIWNAISNEOSW-UHFFFAOYSA-N 2,4-bis(sulfanylidene)-1h-pyrimidine-5-carboxylic acid Chemical group OC(=O)C1=CNC(=S)NC1=S XEJIWNAISNEOSW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GWFOVSGRNGAGDL-FSDSQADBSA-N 2-amino-9-[(1r,2r,3s)-2,3-bis(hydroxymethyl)cyclobutyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1C[C@H](CO)[C@H]1CO GWFOVSGRNGAGDL-FSDSQADBSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
SBJRXHBKPCHGQY-UHFFFAOYSA-N 4,6-dimethylpyrimidine-5-carboxylic acid Chemical group CC1=NC=NC(C)=C1C(O)=O SBJRXHBKPCHGQY-UHFFFAOYSA-N 0.000 description 2
PAZJFXNRVLDLFO-UHFFFAOYSA-N 4-sulfanylmorpholine Chemical compound SN1CCOCC1 PAZJFXNRVLDLFO-UHFFFAOYSA-N 0.000 description 2
MPUCMTUIGIMAEF-UHFFFAOYSA-N 6-cyano-2,4-dimethylpyridine-3-carboxylic acid Chemical compound CC1=CC(C#N)=NC(C)=C1C(O)=O MPUCMTUIGIMAEF-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
229930024421 Adenine Natural products 0.000 description 2
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 2
NGECBQKHSNXDSQ-UHFFFAOYSA-N C1=CC=C2NC=CC2=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 Chemical compound C1=CC=C2NC=CC2=C1.C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 NGECBQKHSNXDSQ-UHFFFAOYSA-N 0.000 description 2
102000001902 CC Chemokines Human genes 0.000 description 2
108010040471 CC Chemokines Proteins 0.000 description 2
102000004500 CCR1 Receptors Human genes 0.000 description 2
108010017319 CCR1 Receptors Proteins 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
208000035473 Communicable disease Diseases 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
108010067306 Fibronectins Proteins 0.000 description 2
102000016359 Fibronectins Human genes 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
208000009329 Graft vs Host Disease Diseases 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
239000012981 Hank's balanced salt solution Substances 0.000 description 2
101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
102000004890 Interleukin-8 Human genes 0.000 description 2
108090001007 Interleukin-8 Proteins 0.000 description 2
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
241000282560 Macaca mulatta Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
241001529936 Murinae Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
108010003533 Viral Envelope Proteins Proteins 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
229960000643 adenine Drugs 0.000 description 2
230000001464 adherent effect Effects 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
230000003409 anti-rejection Effects 0.000 description 2
239000000427 antigen Substances 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
125000005129 aryl carbonyl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000012148 binding buffer Substances 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
230000008859 change Effects 0.000 description 2
239000005482 chemotactic factor Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229960001265 ciclosporin Drugs 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
238000002648 combination therapy Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000001671 coumarin Nutrition 0.000 description 2
229960000956 coumarin Drugs 0.000 description 2
229930182912 cyclosporin Natural products 0.000 description 2
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
230000002950 deficient Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
229960002656 didanosine Drugs 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000007646 directional migration Effects 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229960003722 doxycycline Drugs 0.000 description 2
XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
229960000403 etanercept Drugs 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000835 fiber Substances 0.000 description 2
125000003709 fluoroalkyl group Chemical group 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
238000002825 functional assay Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
229910052737 gold Inorganic materials 0.000 description 2
239000010931 gold Substances 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000002955 immunomodulating agent Substances 0.000 description 2
229940121354 immunomodulator Drugs 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
230000003993 interaction Effects 0.000 description 2
XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
229940096397 interleukin-8 Drugs 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 2
VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
210000004698 lymphocyte Anatomy 0.000 description 2
229960003803 meclofenamic acid Drugs 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
210000004779 membrane envelope Anatomy 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229960000485 methotrexate Drugs 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
210000000214 mouth Anatomy 0.000 description 2
210000003928 nasal cavity Anatomy 0.000 description 2
NQHXCOAXSHGTIA-SKXNDZRYSA-N nelfinavir mesylate Chemical compound CS(O)(=O)=O.CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 NQHXCOAXSHGTIA-SKXNDZRYSA-N 0.000 description 2
229960000689 nevirapine Drugs 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 2
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000007310 pathophysiology Effects 0.000 description 2
229960001639 penicillamine Drugs 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000008024 pharmaceutical diluent Substances 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
210000002706 plastid Anatomy 0.000 description 2
239000011148 porous material Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
230000007115 recruitment Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
229960000329 ribavirin Drugs 0.000 description 2
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 2
229960000311 ritonavir Drugs 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229960001852 saquinavir Drugs 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
230000019491 signal transduction Effects 0.000 description 2
229960002930 sirolimus Drugs 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
125000003003 spiro group Chemical group 0.000 description 2
239000004575 stone Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
210000001179 synovial fluid Anatomy 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
229960001967 tacrolimus Drugs 0.000 description 2
QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 2
BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
230000008719 thickening Effects 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
230000002792 vascular Effects 0.000 description 2
229960002555 zidovudine Drugs 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 description 1
LYYYVSHSLRXPSZ-UHFFFAOYSA-N (2-benzylpiperidin-1-yl)hydrazine Chemical compound C(C1=CC=CC=C1)C1N(CCCC1)NN LYYYVSHSLRXPSZ-UHFFFAOYSA-N 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 description 1
RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 description 1
PZIFPMYXXCAOCC-JWQCQUIFSA-N (2s,3r)-3-(2-carboxyethylsulfanyl)-2-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC(=O)CCS[C@@H]([C@@H](O)C(O)=O)C1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 PZIFPMYXXCAOCC-JWQCQUIFSA-N 0.000 description 1
OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 description 1
HBZBAMXERPYTFS-SECBINFHSA-N (4S)-2-(6,7-dihydro-5H-pyrrolo[3,2-f][1,3]benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)[C@H]1CSC(=N1)c1nc2cc3CCNc3cc2s1 HBZBAMXERPYTFS-SECBINFHSA-N 0.000 description 1
HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
GXINKQQWHLIBJA-UCIBKFKQSA-N (z)-but-2-enedioic acid;(4,6-dimethylpyrimidin-5-yl)-[4-[(3s)-4-[(1r)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone Chemical compound OC(=O)\C=C/C(O)=O.N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C GXINKQQWHLIBJA-UCIBKFKQSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
NHOMNMJPIVXQAD-UHFFFAOYSA-N 1,1'-biphenyl;phthalic acid Chemical class C1=CC=CC=C1C1=CC=CC=C1.OC(=O)C1=CC=CC=C1C(O)=O NHOMNMJPIVXQAD-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
KCLGJWOGTIBHNU-UHFFFAOYSA-N 1,1-difluoroethane fluoroform Chemical compound CC(F)F.FC(F)F KCLGJWOGTIBHNU-UHFFFAOYSA-N 0.000 description 1
PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 1
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
YUCBLVFHJWOYDN-HVLQGHBFSA-N 1,4-bis[(s)-[(2r,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]phthalazine Chemical compound C1=C(OC)C=C2C([C@H](OC=3C4=CC=CC=C4C(O[C@H]([C@@H]4N5CC[C@H]([C@H](C5)CC)C4)C=4C5=CC(OC)=CC=C5N=CC=4)=NN=3)[C@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 YUCBLVFHJWOYDN-HVLQGHBFSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
ASSJTMUEFHUKMJ-UHFFFAOYSA-N 1-acetyl-n-[3-[4-[(4-carbamoylphenyl)methyl]piperidin-1-yl]propyl]-n-(3-chloro-4-methylphenyl)piperidine-4-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(=O)N(C=1C=C(Cl)C(C)=CC=1)CCCN1CCC(CC=2C=CC(=CC=2)C(N)=O)CC1 ASSJTMUEFHUKMJ-UHFFFAOYSA-N 0.000 description 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
VBONNDPACFTZMX-UHFFFAOYSA-N 1-butyl-3-(cyclohexylmethyl)-9-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione Chemical compound N1C(=O)C2(CCN(CC=3C=C4OCCOC4=CC=3)CC2)N(CCCC)C(=O)C1CC1CCCCC1 VBONNDPACFTZMX-UHFFFAOYSA-N 0.000 description 1
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 1
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
NKULBUOBGILEAR-UHFFFAOYSA-N 2,2-difluoroethyl trifluoromethanesulfonate Chemical compound FC(F)COS(=O)(=O)C(F)(F)F NKULBUOBGILEAR-UHFFFAOYSA-N 0.000 description 1
QDKSGHXRHXVMPF-UHFFFAOYSA-N 2,2-dimethylundecane Chemical compound CCCCCCCCCC(C)(C)C QDKSGHXRHXVMPF-UHFFFAOYSA-N 0.000 description 1
XSZKVKMGSAAAJZ-UHFFFAOYSA-N 2,4-dimethylpyridine-3-carboxylic acid Chemical group CC1=CC=NC(C)=C1C(O)=O XSZKVKMGSAAAJZ-UHFFFAOYSA-N 0.000 description 1
LZKZDAMNFOVXBN-UHFFFAOYSA-N 2,6-dimethylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(C)=N1 LZKZDAMNFOVXBN-UHFFFAOYSA-N 0.000 description 1
KLIVRBFRQSOGQI-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzothiepin-3-yl)acetic acid Chemical compound S1CC2=CC=CC=C2C(=O)C2=CC=C(CC(=O)O)C=C12 KLIVRBFRQSOGQI-UHFFFAOYSA-N 0.000 description 1
MYQXHLQMZLTSDB-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2OC(CC)CC2=C1 MYQXHLQMZLTSDB-UHFFFAOYSA-N 0.000 description 1
DCXHLPGLBYHNMU-UHFFFAOYSA-N 2-[1-(4-azidobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(N=[N+]=[N-])C=C1 DCXHLPGLBYHNMU-UHFFFAOYSA-N 0.000 description 1
APBSKHYXXKHJFK-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(C=2C=CC(Cl)=CC=2)=N1 APBSKHYXXKHJFK-UHFFFAOYSA-N 0.000 description 1
TYCOFFBAZNSQOJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC(F)=C1 TYCOFFBAZNSQOJ-UHFFFAOYSA-N 0.000 description 1
JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 description 1
WGDADRBTCPGSDG-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-1,3-oxazol-2-yl]sulfanyl]propanoic acid Chemical compound O1C(SC(C)C(O)=O)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 WGDADRBTCPGSDG-UHFFFAOYSA-N 0.000 description 1
XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
LNGUNERJWIPWSD-UHFFFAOYSA-N 2-diazoacetic acid ethyl acetate Chemical compound C(C)(=O)OCC.[N+](=[N-])=CC(=O)O LNGUNERJWIPWSD-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
HNSBKVZCQMWNPH-UHFFFAOYSA-N 2-methylpropane-1-thiol hydrochloride Chemical compound Cl.CC(C)CS HNSBKVZCQMWNPH-UHFFFAOYSA-N 0.000 description 1
VQNDBXJTIJKJPV-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridine Chemical compound C1=CC=NC2=NNN=C21 VQNDBXJTIJKJPV-UHFFFAOYSA-N 0.000 description 1
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
CGMHPTKJFXHFKV-UHFFFAOYSA-N 3-cyano-2,4-dimethyl-2h-pyridine-3-carboxylic acid Chemical compound CC1N=CC=C(C)C1(C#N)C(O)=O CGMHPTKJFXHFKV-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 1
ROADCYAOHVSOLQ-UHFFFAOYSA-N 3-oxetanone Chemical compound O=C1COC1 ROADCYAOHVSOLQ-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
VDDRQJHPSHDTGX-UHFFFAOYSA-N 3-tert-butyl-2-chloro-2-methylundecane Chemical compound C(C)(C)(C)C(C(C)(C)Cl)CCCCCCCC VDDRQJHPSHDTGX-UHFFFAOYSA-N 0.000 description 1
VYPLQBIHGYKXRS-UHFFFAOYSA-N 4,6-dimethyl-2-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical group CC1=NC(C(F)(F)F)=NC(C)=C1C(O)=O VYPLQBIHGYKXRS-UHFFFAOYSA-N 0.000 description 1
DMYOHBBZDMHYAE-UHFFFAOYSA-N 4,6-dimethylpyrimidine-2-carboxylic acid Chemical group CC1=CC(C)=NC(C(O)=O)=N1 DMYOHBBZDMHYAE-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
SMRZXQLPBYIIND-UHFFFAOYSA-N 4-sulfanyl-1h-pyrimidine-6-thione Chemical compound SC1=CC(=S)NC=N1 SMRZXQLPBYIIND-UHFFFAOYSA-N 0.000 description 1
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 description 1
XDUARVBJHGGPEP-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NOC=1C(F)(F)F XDUARVBJHGGPEP-UHFFFAOYSA-N 0.000 description 1
ATCRIOJPQXDFNY-ZETCQYMHSA-N 6-chloro-2-(1-furo[2,3-c]pyridin-5-yl-ethylsulfanyl)-pyrimidin-4-ylamine Chemical compound S([C@@H](C)C=1N=CC=2OC=CC=2C=1)C1=NC(N)=CC(Cl)=N1 ATCRIOJPQXDFNY-ZETCQYMHSA-N 0.000 description 1
IXJCHVMUTFCRBH-SDUHDBOFSA-N 7-[(1r,2s,3e,5z)-10-(4-acetyl-3-hydroxy-2-propylphenoxy)-1-hydroxy-1-[3-(trifluoromethyl)phenyl]deca-3,5-dien-2-yl]sulfanyl-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCC\C=C/C=C/[C@@H]([C@H](O)C=1C=C(C=CC=1)C(F)(F)F)SC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 IXJCHVMUTFCRBH-SDUHDBOFSA-N 0.000 description 1
CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
108700028369 Alleles Proteins 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
XHVAWZZCDCWGBK-WYRLRVFGSA-M Aurothioglucose Chemical compound OC[C@H]1O[C@H](S[Au])[C@H](O)[C@@H](O)[C@@H]1O XHVAWZZCDCWGBK-WYRLRVFGSA-M 0.000 description 1
235000017166 Bambusa arundinacea Nutrition 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
MALHMPVUZHQAKX-UHFFFAOYSA-N C(CCCCCCCCC)C1(NC(CCC1)(CCCCCCCCCC)CCCCCCCCCC)CCCCCCCCCC Chemical compound C(CCCCCCCCC)C1(NC(CCC1)(CCCCCCCCCC)CCCCCCCCCC)CCCCCCCCCC MALHMPVUZHQAKX-UHFFFAOYSA-N 0.000 description 1
102100023702 C-C motif chemokine 13 Human genes 0.000 description 1
101710112613 C-C motif chemokine 13 Proteins 0.000 description 1
102100032366 C-C motif chemokine 7 Human genes 0.000 description 1
101710155834 C-C motif chemokine 7 Proteins 0.000 description 1
102100034871 C-C motif chemokine 8 Human genes 0.000 description 1
101710155833 C-C motif chemokine 8 Proteins 0.000 description 1
102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
101710082513 C-X-C chemokine receptor type 4 Proteins 0.000 description 1
SUCVTBYCBHLMRY-UHFFFAOYSA-N C1=C(N=CN=C1CF)CF Chemical compound C1=C(N=CN=C1CF)CF SUCVTBYCBHLMRY-UHFFFAOYSA-N 0.000 description 1
VWRQZMSSWYCZTG-UHFFFAOYSA-N CC1(C(N(N(C=CC1)C)C)(C)C)C.[Li] Chemical compound CC1(C(N(N(C=CC1)C)C)(C)C)C.[Li] VWRQZMSSWYCZTG-UHFFFAOYSA-N 0.000 description 1
KXENXGBRRCMGPC-MGCOHNPYSA-N CCO[C@H]1CC[C@H](C(=O)OCC)CC1 Chemical compound CCO[C@H]1CC[C@H](C(=O)OCC)CC1 KXENXGBRRCMGPC-MGCOHNPYSA-N 0.000 description 1
WLRJHFIRCVDODH-UHFFFAOYSA-L CCO[Sb](O)(Cl)=O Chemical compound CCO[Sb](O)(Cl)=O WLRJHFIRCVDODH-UHFFFAOYSA-L 0.000 description 1
101150017501 CCR5 gene Proteins 0.000 description 1
108050006947 CXC Chemokine Proteins 0.000 description 1
102000019388 CXC chemokine Human genes 0.000 description 1
108010061299 CXCR4 Receptors Proteins 0.000 description 1
102000012000 CXCR4 Receptors Human genes 0.000 description 1
101100504320 Caenorhabditis elegans mcp-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
102000000844 Cell Surface Receptors Human genes 0.000 description 1
108010001857 Cell Surface Receptors Proteins 0.000 description 1
208000035484 Cellulite Diseases 0.000 description 1
229940122444 Chemokine receptor antagonist Drugs 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
YAYPTFVTLSOODF-UHFFFAOYSA-N ClNC(CCC)N Chemical compound ClNC(CCC)N YAYPTFVTLSOODF-UHFFFAOYSA-N 0.000 description 1
OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
206010011469 Crying Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
102100030497 Cytochrome c Human genes 0.000 description 1
210000004128 D cell Anatomy 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
206010012438 Dermatitis atopic Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010013710 Drug interaction Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 1
101710091045 Envelope protein Proteins 0.000 description 1
102100023688 Eotaxin Human genes 0.000 description 1
101710139422 Eotaxin Proteins 0.000 description 1
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
FLXIYPAHUDHXGX-UHFFFAOYSA-N FC(S(=O)(=O)O)(F)F.FC(C)F Chemical compound FC(S(=O)(=O)O)(F)F.FC(C)F FLXIYPAHUDHXGX-UHFFFAOYSA-N 0.000 description 1
RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 description 1
DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 1
208000037357 HIV infectious disease Diseases 0.000 description 1
241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 description 1
108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 1
108010002350 Interleukin-2 Proteins 0.000 description 1
UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
102000003820 Lipoxygenases Human genes 0.000 description 1
108090000128 Lipoxygenases Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
102000009571 Macrophage Inflammatory Proteins Human genes 0.000 description 1
108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 1
108010090054 Membrane Glycoproteins Proteins 0.000 description 1
102000012750 Membrane Glycoproteins Human genes 0.000 description 1
102000018697 Membrane Proteins Human genes 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
102000014962 Monocyte Chemoattractant Proteins Human genes 0.000 description 1
108010064136 Monocyte Chemoattractant Proteins Proteins 0.000 description 1
206010048723 Multiple-drug resistance Diseases 0.000 description 1
101000978374 Mus musculus C-C motif chemokine 12 Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OKLUZMUKXYWEGD-UHFFFAOYSA-N N-bromobutan-1-imine Chemical compound CCCC=NBr OKLUZMUKXYWEGD-UHFFFAOYSA-N 0.000 description 1
LMRSEVSTKGLDNY-UHFFFAOYSA-N N1C(=O)NC=2N=CNC2C1=O.CC1=CC=CC=C1 Chemical compound N1C(=O)NC=2N=CNC2C1=O.CC1=CC=CC=C1 LMRSEVSTKGLDNY-UHFFFAOYSA-N 0.000 description 1
229940124821 NNRTIs Drugs 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
JNTSWGACBKZCSR-UHFFFAOYSA-N OC1=C(C(=O)O)C=CC=C1.C(C)(=N)N Chemical compound OC1=C(C(=O)O)C=CC=C1.C(C)(=N)N JNTSWGACBKZCSR-UHFFFAOYSA-N 0.000 description 1
208000001388 Opportunistic Infections Diseases 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
206010034133 Pathogen resistance Diseases 0.000 description 1
206010049752 Peau d'orange Diseases 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
244000082204 Phyllostachys viridis Species 0.000 description 1
235000015334 Phyllostachys viridis Nutrition 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
101710188315 Protein X Proteins 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
229940123934 Reductase inhibitor Drugs 0.000 description 1
108700008625 Reporter Genes Proteins 0.000 description 1
241000219061 Rheum Species 0.000 description 1
NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
101000874347 Streptococcus agalactiae IgA FC receptor Proteins 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
101800001690 Transmembrane protein gp41 Proteins 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
229940118555 Viral entry inhibitor Drugs 0.000 description 1
YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 description 1
WCNUIBRUGZPMFC-UHFFFAOYSA-I [Br-].[Mg+2].[Y+3].[Br-].[Br-].[Br-].[Br-] Chemical compound [Br-].[Mg+2].[Y+3].[Br-].[Br-].[Br-].[Br-] WCNUIBRUGZPMFC-UHFFFAOYSA-I 0.000 description 1
CDYHICOURBNBAV-UHFFFAOYSA-N [Cl].COC=O Chemical compound [Cl].COC=O CDYHICOURBNBAV-UHFFFAOYSA-N 0.000 description 1
SLEGPTUZZMEOPB-UHFFFAOYSA-N [Na].C(CCCCCCCCC)N Chemical compound [Na].C(CCCCCCCCC)N SLEGPTUZZMEOPB-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
229960004748 abacavir Drugs 0.000 description 1
WMHSRBZIJNQHKT-FFKFEZPRSA-N abacavir sulfate Chemical compound OS(O)(=O)=O.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 WMHSRBZIJNQHKT-FFKFEZPRSA-N 0.000 description 1
229960004892 acemetacin Drugs 0.000 description 1
FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229960002964 adalimumab Drugs 0.000 description 1
WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 description 1
229960003205 adefovir dipivoxil Drugs 0.000 description 1
229960005142 alclofenac Drugs 0.000 description 1
ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000000676 alkoxyimino group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000007815 allergy Effects 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
108010074587 aminooxypentane-RANTES Proteins 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
238000011225 antiretroviral therapy Methods 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
229940059756 arava Drugs 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012911 assay medium Substances 0.000 description 1
238000006256 asymmetric dihydroxylation reaction Methods 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 1
229960005207 auranofin Drugs 0.000 description 1
229960001799 aurothioglucose Drugs 0.000 description 1
229940022777 azasan Drugs 0.000 description 1
229960002170 azathioprine Drugs 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000011425 bamboo Substances 0.000 description 1
229960004669 basiliximab Drugs 0.000 description 1
210000003651 basophil Anatomy 0.000 description 1
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
229940092705 beclomethasone Drugs 0.000 description 1
229960005430 benoxaprofen Drugs 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
229960002537 betamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000003851 biochemical process Effects 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000001851 biosynthetic effect Effects 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
238000007664 blowing Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229950005608 bucloxic acid Drugs 0.000 description 1
IJTPQQVCKPZIMV-UHFFFAOYSA-N bucloxic acid Chemical compound ClC1=CC(C(=O)CCC(=O)O)=CC=C1C1CCCCC1 IJTPQQVCKPZIMV-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000001354 calcination Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
230000003185 calcium uptake Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
229960003184 carprofen Drugs 0.000 description 1
IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 description 1
238000004517 catalytic hydrocracking Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229960000590 celecoxib Drugs 0.000 description 1
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
238000002737 cell proliferation kit Methods 0.000 description 1
229940107810 cellcept Drugs 0.000 description 1
230000036232 cellulite Effects 0.000 description 1
CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 1
229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
239000002975 chemoattractant Substances 0.000 description 1
239000002559 chemokine receptor antagonist Substances 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
229950010886 clidanac Drugs 0.000 description 1
238000010549 co-Evaporation Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
229940088900 crixivan Drugs 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000011461 current therapy Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
LHQRDAIAWDPZGH-UHFFFAOYSA-N cyclohexylhydrazine Chemical compound NNC1CCCCC1 LHQRDAIAWDPZGH-UHFFFAOYSA-N 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
102000003675 cytokine receptors Human genes 0.000 description 1
108010057085 cytokine receptors Proteins 0.000 description 1
229960002806 daclizumab Drugs 0.000 description 1
229960005319 delavirdine Drugs 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
210000004443 dendritic cell Anatomy 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
229960000633 dextran sulfate Drugs 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
229960001259 diclofenac Drugs 0.000 description 1
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
ZOGHDTBRWUEJDP-UHFFFAOYSA-N diethylalumanylium;cyanide Chemical compound N#[C-].CC[Al+]CC ZOGHDTBRWUEJDP-UHFFFAOYSA-N 0.000 description 1
HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
229960000616 diflunisal Drugs 0.000 description 1
RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical class FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
150000002013 dioxins Chemical class 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
230000026058 directional locomotion Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940075117 droxia Drugs 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
238000009510 drug design Methods 0.000 description 1
230000008406 drug-drug interaction Effects 0.000 description 1
229960003804 efavirenz Drugs 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
229940073621 enbrel Drugs 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
229940072253 epivir Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000003172 expectorant agent Substances 0.000 description 1
230000003419 expectorant effect Effects 0.000 description 1
229940066493 expectorants Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000013604 expression vector Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000001815 facial effect Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
229960001395 fenbufen Drugs 0.000 description 1
ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
229950006236 fenclofenac Drugs 0.000 description 1
IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 description 1
229950011481 fenclozic acid Drugs 0.000 description 1
229960001419 fenoprofen Drugs 0.000 description 1
229960002679 fentiazac Drugs 0.000 description 1
229960000489 feprazone Drugs 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
229950007979 flufenisal Drugs 0.000 description 1
239000012530 fluid Substances 0.000 description 1
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229960002464 fluoxetine Drugs 0.000 description 1
229950001284 fluprofen Drugs 0.000 description 1
229960002390 flurbiprofen Drugs 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
230000004907 flux Effects 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000004052 folic acid antagonist Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229950010931 furofenac Drugs 0.000 description 1
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002344 gold compounds Chemical class 0.000 description 1
229940015045 gold sodium thiomalate Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
229940048921 humira Drugs 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
229950009183 ibufenac Drugs 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000036737 immune function Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000003018 immunoassay Methods 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
229940125721 immunosuppressive agent Drugs 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000005414 inactive ingredient Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229960001936 indinavir Drugs 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
229960004187 indoprofen Drugs 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229960000598 infliximab Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229940088976 invirase Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229950000831 iralukast Drugs 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 description 1
229950011455 isoxepac Drugs 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960001627 lamivudine Drugs 0.000 description 1
229950004697 lasinavir Drugs 0.000 description 1
229960000681 leflunomide Drugs 0.000 description 1
239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
238000000670 ligand binding assay Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
229950005339 lobucavir Drugs 0.000 description 1
KBEMFSMODRNJHE-JFWOZONXSA-N lodenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@@H]1F KBEMFSMODRNJHE-JFWOZONXSA-N 0.000 description 1
238000012153 long-term therapy Methods 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000003468 luciferase reporter gene assay Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000002932 luster Substances 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
210000003071 memory t lymphocyte Anatomy 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
SOBKMRUKIGDINL-UHFFFAOYSA-N methyl 2-chlorodecanoate Chemical compound CCCCCCCCC(Cl)C(=O)OC SOBKMRUKIGDINL-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960004584 methylprednisolone Drugs 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-O methylsulfide anion Chemical compound [SH2+]C LSDPWZHWYPCBBB-UHFFFAOYSA-O 0.000 description 1
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
210000005063 microvascular endothelium Anatomy 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
OJGQFYYLKNCIJD-UHFFFAOYSA-N miroprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CN(C=CC=C2)C2=N1 OJGQFYYLKNCIJD-UHFFFAOYSA-N 0.000 description 1
229950006616 miroprofen Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229960005285 mofebutazone Drugs 0.000 description 1
REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229930003658 monoterpene Natural products 0.000 description 1
150000002773 monoterpene derivatives Chemical class 0.000 description 1
235000002577 monoterpenes Nutrition 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
229940051866 mouthwash Drugs 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
230000035772 mutation Effects 0.000 description 1
RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 1
229960004866 mycophenolate mofetil Drugs 0.000 description 1
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 1
YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960000916 niflumic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229940072250 norvir Drugs 0.000 description 1
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006772 olefination reaction Methods 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
230000008520 organization Effects 0.000 description 1
JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
229960002739 oxaprozin Drugs 0.000 description 1
OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000009522 phase III clinical trial Methods 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000006187 pill Substances 0.000 description 1
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical group NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
229960002702 piroxicam Drugs 0.000 description 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
229960000851 pirprofen Drugs 0.000 description 1
PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 description 1
229950011515 pobilukast Drugs 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
239000004626 polylactic acid Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical compound [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 description 1
UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
229960004583 pranlukast Drugs 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
229940072288 prograf Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
NUBSZFGESDICNN-UHFFFAOYSA-N propan-2-yl chlorate Chemical compound CC(C)OCl(=O)=O NUBSZFGESDICNN-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
JVANLUCASVHWEW-UHFFFAOYSA-N pyridazine Chemical compound N1=C=C=C=C=N1 JVANLUCASVHWEW-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000012797 qualification Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
229940099538 rapamune Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
108010043277 recombinant soluble CD4 Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229940116176 remicade Drugs 0.000 description 1
238000009877 rendering Methods 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
230000010076 replication Effects 0.000 description 1
229940063627 rescriptor Drugs 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229940064914 retrovir Drugs 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
229940063122 sandimmune Drugs 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229940115586 simulect Drugs 0.000 description 1
239000002356 single layer Substances 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
AGHLUVOCTHWMJV-UHFFFAOYSA-J sodium;gold(3+);2-sulfanylbutanedioate Chemical compound [Na+].[Au+3].[O-]C(=O)CC(S)C([O-])=O.[O-]C(=O)CC(S)C([O-])=O AGHLUVOCTHWMJV-UHFFFAOYSA-J 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
210000002325 somatostatin-secreting cell Anatomy 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
229950005175 sudoxicam Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
229960001940 sulfasalazine Drugs 0.000 description 1
NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229960000894 sulindac Drugs 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000010648 susceptibility to HIV infection Diseases 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
229940054565 sustiva Drugs 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
210000001258 synovial membrane Anatomy 0.000 description 1
210000005222 synovial tissue Anatomy 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
OYRWWTPZWOPIOO-SECBINFHSA-N tert-butyl (3r)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](CCO)C1 OYRWWTPZWOPIOO-SECBINFHSA-N 0.000 description 1
OXSSNJRGXRJNPX-UHFFFAOYSA-N tert-butyl 4-methylpiperidine-1-carboxylate Chemical group CC1CCN(C(=O)OC(C)(C)C)CC1 OXSSNJRGXRJNPX-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
XRFRTDKENRGSSX-UHFFFAOYSA-J tetrasodium;3-[[4-[[4-[(4,8-disulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]carbamoylamino]-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N=NC3=CC=C(NC(=O)NC=4C=C(C)C(N=NC=5C=C6C(=CC=CC6=C(C=5)S([O-])(=O)=O)S([O-])(=O)=O)=CC=4)C=C3C)=CC(S([O-])(=O)=O)=C21 XRFRTDKENRGSSX-UHFFFAOYSA-J 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229960001312 tiaprofenic acid Drugs 0.000 description 1
229950002345 tiopinac Drugs 0.000 description 1
229950006150 tioxaprofen Drugs 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229960002905 tolfenamic acid Drugs 0.000 description 1
YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
229960001017 tolmetin Drugs 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
238000011295 triple combination therapy Methods 0.000 description 1
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000012795 verification Methods 0.000 description 1
229940023080 viracept Drugs 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
229940098802 viramune Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229960004764 zafirlukast Drugs 0.000 description 1
229940087450 zerit Drugs 0.000 description 1
229940052255 ziagen Drugs 0.000 description 1
229950007802 zidometacin Drugs 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Physical Education & Sports Medicine (AREA)
Oncology (AREA)
Rheumatology (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
AIDS & HIV (AREA)
Heart & Thoracic Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

TW097110847A 2007-03-29 2008-03-26 Heterocyclic antiviral compounds TW200902020A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US92069407P	2007-03-29	2007-03-29

Publications (1)

Publication Number	Publication Date
TW200902020A true TW200902020A (en)	2009-01-16

Family

ID=39535486

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW097110847A TW200902020A (en)	2007-03-29	2008-03-26	Heterocyclic antiviral compounds

Country Status (15)

Country	Link
US (1)	US7625891B2 (pt)
EP (1)	EP2142555A1 (pt)
JP (1)	JP2010522707A (pt)
KR (1)	KR20090127298A (pt)
CN (1)	CN101646679A (pt)
AR (1)	AR065854A1 (pt)
AU (1)	AU2008233930A1 (pt)
BR (1)	BRPI0809646A2 (pt)
CA (1)	CA2682639A1 (pt)
CL (1)	CL2008000863A1 (pt)
IL (1)	IL200661A0 (pt)
MX (1)	MX2009010503A (pt)
PE (1)	PE20090183A1 (pt)
TW (1)	TW200902020A (pt)
WO (1)	WO2008119663A1 (pt)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5451611B2 (ja) *	2007-07-26	2014-03-26	ヴァイティーファーマシューティカルズ，インコーポレイテッド	１１β−ヒドロキシステロイドデヒドロゲナーゼ１のサイクリックインヒビター
WO2009037168A1 (en) *	2007-09-19	2009-03-26	F. Hoffmann-La Roche Ag	Heterocyclic antiviral compounds
AR069207A1 (es) *	2007-11-07	2010-01-06	Vitae Pharmaceuticals Inc	Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1
CA2708303A1 (en)	2007-12-11	2009-06-18	Vitae Pharmaceuticals, Inc.	Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1
TW200934490A (en) *	2008-01-07	2009-08-16	Vitae Pharmaceuticals Inc	Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1
WO2009094169A1 (en)	2008-01-24	2009-07-30	Vitae Pharmaceuticals, Inc.	Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1
CA2714532A1 (en) *	2008-02-11	2009-08-20	Vitae Pharmaceuticals, Inc.	1,3-oxazepan-2-one and 1,3-diazepan-2-one inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1
US8598160B2 (en) *	2008-02-15	2013-12-03	Vitae Pharmaceuticals, Inc.	Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
CA2718264A1 (en) *	2008-03-18	2009-09-24	Vitae Pharmaceuticals, Inc.	Inhibitors of 11beta-hydroxysteroid dehydrogenase type 1
EP2291370B1 (en)	2008-05-01	2013-11-27	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
TW201004945A (en)	2008-05-01	2010-02-01	Vitae Pharmaceuticals Inc	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
KR20110002492A (ko)	2008-05-01	2011-01-07	비타이 파마슈티컬즈, 인코포레이티드	11베타-하이드록시스테로이드 탈수소효소 1의 고리형 억제제
CA2723032A1 (en) *	2008-05-01	2009-11-05	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8846668B2 (en)	2008-07-25	2014-09-30	Vitae Pharmaceuticals, Inc.	Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
WO2010011314A1 (en)	2008-07-25	2010-01-28	Boehringer Ingelheim International Gmbh	Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
CA2737645A1 (en)	2008-09-25	2010-04-01	Boehringer Ingelheim International Gmbh	Compounds which selectively modulate the cb2 receptor
JP5679997B2 (ja)	2009-02-04	2015-03-04	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	１１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状阻害剤
UA109255C2 (ru)	2009-04-30	2015-08-10	Берінгер Інгельхайм Інтернешнл Гмбх	Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1
WO2011011123A1 (en)	2009-06-11	2011-01-27	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure
WO2011002910A1 (en)	2009-07-01	2011-01-06	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8329735B2 (en)	2010-03-05	2012-12-11	Boehringer Ingelheim International Gmbh	Tetrazole compounds which selectively modulate the CB2 receptor
EP2582698B1 (en)	2010-06-16	2016-09-14	Vitae Pharmaceuticals, Inc.	Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
WO2011161128A1 (en)	2010-06-25	2011-12-29	Boehringer Ingelheim International Gmbh	Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders
CA2813671A1 (en)	2010-11-02	2012-05-10	Boehringer Ingelheim International Gmbh	Pharmaceutical combinations for the treatment of metabolic disorders
EP2680850B1 (en)	2011-03-04	2018-05-23	Newgen Therapeutics, Inc.	Alkyne substituted quinazoline compound and methods of use
CN102918029B (zh)	2011-05-17	2015-06-17	江苏康缘药业股份有限公司	4-苯胺-6-丁烯酰胺-7-烷醚喹唑啉衍生物及其制备方法和用途
EP3395804B1 (en) *	2016-09-08	2020-05-13	Gachon University of Industry-Academic Cooperation Foundation	Novel spiroquinone derivative compound, production method thereof, and pharmaceutical composition for preventing or treating neurological disorders which contains same as active ingredient
CN109012748B (zh) *	2018-07-27	2021-03-16	安徽师范大学	吡啶取代吡咯基稀土金属催化剂及其制备方法和应用

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL127065C (pt)	1964-04-22
HU204529B (en)	1989-08-10	1992-01-28	Richter Gedeon Vegyeszet	Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them
WO1997011940A1 (en)	1995-09-29	1997-04-03	Eli Lilly And Company	Spiro compounds as inhibitors of fibrinogen-dependent platelet aggregation
SK286641B6 (sk)	1999-05-04	2009-03-05	Schering Corporation	Piperazínové deriváty užitočné ako CCR5 antagonisty, farmaceutické prípravky s ich obsahom a ich použitie
US6689765B2 (en)	1999-05-04	2004-02-10	Schering Corporation	Piperazine derivatives useful as CCR5 antagonists
US6391865B1 (en)	1999-05-04	2002-05-21	Schering Corporation	Piperazine derivatives useful as CCR5 antagonists
PL203117B1 (pl)	1999-05-04	2009-08-31	Schering Corp	Piperydynopiperydynowa pochodna użyteczna jako antagonista CCR5, zawierająca ją kompozycja farmaceutyczna i jej zastosowanie
NZ519183A (en)	1999-12-03	2005-02-25	Ono Pharmaceutical Co	Triazaspiro[5.5]undecane derivatives and pharmaceutical compositions comprising thereof, as an active ingredient
AU2001230537A1 (en)	2000-02-01	2001-08-14	Daiichi Pharmaceutical Co., Ltd.	Pyridoxazine derivatives
DK1390372T3 (da)	2001-05-14	2008-09-15	Hoffmann La Roche	1-oxa-3,9-diaza-spiro '5,5]undecan-2-on-derivater og anvendelse deraf som neurokininreceptorantagonist
NZ533567A (en)	2001-12-28	2007-06-29	Acadia Pharm Inc	Spiroazacyclic compounds as monoamine receptor for modulating 5-HT2A receptor-mediated events
EP1716156A2 (en) *	2004-02-10	2006-11-02	F.Hoffmann-La Roche Ag	Chemokine ccr5 receptor modulators
WO2007085567A2 (en) *	2006-01-30	2007-08-02	F. Hoffmann-La Roche Ag	Synergistic compositions for treating hiv

2008
- 2008-03-18 BR BRPI0809646-5A patent/BRPI0809646A2/pt not_active Application Discontinuation
- 2008-03-18 CN CN200880010622A patent/CN101646679A/zh active Pending
- 2008-03-18 KR KR1020097020226A patent/KR20090127298A/ko not_active Withdrawn
- 2008-03-18 AU AU2008233930A patent/AU2008233930A1/en not_active Abandoned
- 2008-03-18 WO PCT/EP2008/053238 patent/WO2008119663A1/en not_active Ceased
- 2008-03-18 EP EP08717970A patent/EP2142555A1/en not_active Withdrawn
- 2008-03-18 MX MX2009010503A patent/MX2009010503A/es unknown
- 2008-03-18 CA CA002682639A patent/CA2682639A1/en not_active Abandoned
- 2008-03-18 JP JP2010500218A patent/JP2010522707A/ja active Pending
- 2008-03-26 PE PE2008000546A patent/PE20090183A1/es not_active Application Discontinuation
- 2008-03-26 TW TW097110847A patent/TW200902020A/zh unknown
- 2008-03-26 CL CL2008000863A patent/CL2008000863A1/es unknown
- 2008-03-27 AR ARP080101248A patent/AR065854A1/es unknown
- 2008-03-28 US US12/079,746 patent/US7625891B2/en not_active Expired - Fee Related
2009
- 2009-09-01 IL IL200661A patent/IL200661A0/en unknown

Also Published As

Publication number	Publication date
US7625891B2 (en)	2009-12-01
PE20090183A1 (es)	2009-03-12
BRPI0809646A2 (pt)	2014-09-23
CN101646679A (zh)	2010-02-10
CL2008000863A1 (es)	2008-11-07
JP2010522707A (ja)	2010-07-08
CA2682639A1 (en)	2008-10-09
KR20090127298A (ko)	2009-12-10
AR065854A1 (es)	2009-07-08
IL200661A0 (en)	2010-05-17
EP2142555A1 (en)	2010-01-13
AU2008233930A1 (en)	2008-10-09
US20080249087A1 (en)	2008-10-09
WO2008119663A1 (en)	2008-10-09
MX2009010503A (es)	2009-10-19

Publication	Publication Date	Title
US7625891B2 (en)	2009-12-01	Heterocylic antiviral compounds
KR100863854B1 (ko)	2008-10-15	케모카인 ｃｃｒ5 수용체 조절제
ES2345130T3 (es)	2010-09-15	Derivados de octahidropirrolo(3,4-c)pirrol y su uso como antiviricos.
RS51701B (sr)	2011-10-31	Azabicikloalkani kao modulatori ccr5
JP2008501743A (ja)	2008-01-24	複素環式抗ウイルス性化合物
US20090281133A1 (en)	2009-11-12	Heterocyclic antiviral compounds
JP2024515545A (ja)	2024-04-10	がん治療のためのピリジニル置換オキソイソインドリン化合物
TW200916460A (en)	2009-04-16	Heterocyclic antiviral compounds
US20090093501A1 (en)	2009-04-09	Heterocyclic antiviral compounds
CN1898231B (zh)	2010-10-27	用作趋化因子受体抑制剂的双六氢吡啶衍生物
US20080081803A1 (en)	2008-04-03	Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity
MXPA06008948A (en)	2006-12-13	Chemokine ccr5 receptor modulators
EA045973B1 (ru)	2024-01-24	Ингибиторы секреции белка на основе триазациклододекансульфонамида ("tcd")